14 women Don Draper has romanced

By By Business Insider

on April 5, 2013 11:57 AM

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Formerly a model, Betty was Don's first wife. Increasingly manic-depressive and discontent, Betty spent much of her marriage to Don stuck in the suburbs as Don gallivanted about in NYC.
After catching on to Don's promiscuity, she left him for Henry Francis, an aide to Nelson Rockefeller. She married Francis right after she had Don's third child, Eugene, becoming Betty Francis.
Played by January Jones.

Formerly a model, Betty was Don's first wife. Increasingly manic-depressive and discontent, Betty spent much of her marriage to Don stuck in the suburbs as Don gallivanted about in NYC.
After catching on to ... more

Midge is an artist and a free-spirited pothead whom we first meet early in Season 1. She rejects Don's dreams of domesticating her, and turns down his invitation to elope to Paris.
In Season 4, she reappears as a heroin addict and wife to a failed playwright. She tries to get drug money out of Don — Don obliges, buying one of her paintings out of sympathy.
Played by Rosemarie Dewitt. less

Midge is an artist and a free-spirited pothead whom we first meet early in Season 1. She rejects Don's dreams of domesticating her, and turns down his invitation to elope to Paris.
In Season 4, she reappears ... more

Midge is an artist and a free-spirited pothead whom we first meet... Photo-4427498.59799 - StamfordAdvocate

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Rachel is the head of Menken's Department store, a client of Sterling Cooper. Initially, she is against a romance with Don, a married man, but she eventually caves.
Don, apparently in love, asks her to run away to L.A. with him, but she shoots him down. In Season 2, Don sees her in a restaurant, where she introduces him to her new husband.
Played by Maggie Siff. less

Rachel is the head of Menken's Department store, a client of Sterling Cooper. Initially, she is against a romance with Don, a married man, but she eventually caves.
Don, apparently in love, asks her to run ... more

Rachel is the head of Menken's Department store, a client of... Photo-4427499.59799 - StamfordAdvocate

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Bobbie is the wife of comedian Jimmy Barrett. She and Don begin their affair during a dinner with their spouses. The affair gets violent when Jimmy finds out about it. Betty also learns about the affair and confronts Don.
Played by Melinda McGraw. less

Bobbie is the wife of comedian Jimmy Barrett. She and Don begin their affair during a dinner with their spouses. The affair gets violent when Jimmy finds out about it. Betty also learns about the affair and ... more

Bobbie is the wife of comedian Jimmy Barrett. She and Don begin... Photo-4427500.59799 - StamfordAdvocate

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While on a business trip in California during Season 2, Don has a fling with a wealthy woman named Joy. After a weekend together, she invites him to stay, but Don ducks out of her glamorous Palm Springs accommodations to return to New York.
Played by Laura Ramsey less

While on a business trip in California during Season 2, Don has a fling with a wealthy woman named Joy. After a weekend together, she invites him to stay, but Don ducks out of her glamorous Palm Springs ... more

While on a business trip in California during Season 2, Don has a... Photo-4427502.59799 - StamfordAdvocate

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Anna is the real Don Draper's wife. Upon learning that Don has stolen her dead husband's identity, she becomes his closest confidante. Their relationship is never romantic, but it's arguably more important than any other relationship Don has with a woman.
Anna dies of cancer in Season 4, leaving Don devastated. He calls her "the only person in the world who really knew me."
Played by Melinda Page Hamilton. less

Anna is the real Don Draper's wife. Upon learning that Don has stolen her dead husband's identity, she becomes his closest confidante. Their relationship is never romantic, but it's arguably more important than ... more

Shelly is a TWA stewardess Don meets on a flight to Baltimore in the first episode of Season 3. Despite her engagement, they have a one-night stand in a hotel room.
They are interrupted by a fire alarm, after which Shelly disappears, never to be seen again. Don keeps her pin-on wings and gives them to his daughter Sally.
Played by Sunny Mabrey. less

Shelly is a TWA stewardess Don meets on a flight to Baltimore in the first episode of Season 3. Despite her engagement, they have a one-night stand in a hotel room.
They are interrupted by a fire alarm, after ... more

Shelly is a TWA stewardess Don meets on a flight to Baltimore in... Photo-4427504.59799 - StamfordAdvocate

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Sally's idealistic third-grade teacher is initially okay with a secret affair, but later switches gears and decides she wants it publicized. Don cuts it off promptly, not least because he is confronted by Betty about his identity.
Played by Abigail Spencer. less

Sally's idealistic third-grade teacher is initially okay with a secret affair, but later switches gears and decides she wants it publicized. Don cuts it off promptly, not least because he is confronted by Betty ... more

Candace is a prostitute Don visits for rough sex. In one scene from the episode "Public Relations," she slaps Don in the face. "Harder," he says.
Played by Erin Cummings.

Candace is a prostitute Don visits for rough sex. In one scene from the episode "Public Relations," she slaps Don in the face. "Harder," he says.
Played by Erin Cummings.

Candace is a prostitute Don visits for rough sex. In one scene from... Photo-4427506.59799 - StamfordAdvocate

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Following Don and Betty's divorce, Roger Sterling's wife, Jane, hooks Don up with her friend Bethany, who turns out to be a pretty, but dull, companion.
She complains to Don that she rarely sees him, but she does manage to irk Betty when they run into Betty and her new husband at dinner. Their relationship is short-lived.
Played by Anna Camp. less

Following Don and Betty's divorce, Roger Sterling's wife, Jane, hooks Don up with her friend Bethany, who turns out to be a pretty, but dull, companion.
She complains to Don that she rarely sees him, but she ... more

Allison is Don's first secretary at Sterling Cooper and later at Sterling Cooper Draper Pryce. After the office Christmas party early in Season 4, Allison goes over to Don's to take him the keys he forgot. Predictably, the visit becomes romantic.
Allison is heartbroken that he won't acknowledge their one-night stand the next day. She soon resigns and asks Don for a recommendation; he tells her to write one for herself that he will sign. She storms out, furious. She hasn't returned since.
Played by Alexa Allemani. less

Allison is Don's first secretary at Sterling Cooper and later at Sterling Cooper Draper Pryce. After the office Christmas party early in Season 4, Allison goes over to Don's to take him the keys he forgot. ... more

Allison is Don's first secretary at Sterling Cooper and later... Photo-4427508.59799 - StamfordAdvocate

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After winning at the Clios, Don celebrates hard for a few days. In this time, he gets around without remembering much.
He drunkenly sleeps with two women in one night, going to bed with an unnamed jingle writer and waking up with a disheveled diner waitress named Doris, to whom he introduced himself as Dick (his real name). Double whoops.
Played by Becky Wahlstrom. less

After winning at the Clios, Don celebrates hard for a few days. In this time, he gets around without remembering much.
He drunkenly sleeps with two women in one night, going to bed with an unnamed jingle ... more

After winning at the Clios, Don celebrates hard for a few days. In... Photo-4427509.59799 - StamfordAdvocate

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Faye is a "modern" woman — independent and career-oriented, she is a successful consultant to Sterling Cooper Draper Pryce. She initially turns Don down after his success at the Clios. Later in Season 4, however, they start a secret relationship.
Don cuts off his fling with Faye by announcing his engagement. Faye is upset, and tells Don she hopes his fiancée knows that he only likes "the beginning of things."
Played by Cara Buono. less

Faye is a "modern" woman — independent and career-oriented, she is a successful consultant to Sterling Cooper Draper Pryce. She initially turns Don down after his success at the Clios. Later in Season 4, ... more

Formerly Megan Calvet, the new Mrs. Draper is Don's receptionist turned copywriter turned commercial actress turned wife.
Megan has a great record taking care of Don's kids, traveling to California with the family in Season 4 to help out. Don proposes at the end of season four.
Played by Jessica Pare. less

Formerly Megan Calvet, the new Mrs. Draper is Don's receptionist turned copywriter turned commercial actress turned wife.
Megan has a great record taking care of Don's kids, traveling to California with the ... more